Help Center / Settlements and Pay

Year-End 1099s

Generate 1099-NEC recipient copies for owner-operators, lease operators and fleet owners from their settlements, and download them as PDFs. CloudTMS does not file with the IRS for you.

Where in CloudTMS: /settlements?tab=year-end, /drivers/[id]

Who Appears and Why

The Year-End / 1099s tab lists owner-operators, lease operators and fleet owners for the selected Tax year. YTD Comp comes from their settlements for that year. Recipients at or above the reporting threshold are listed under Eligible for 1099-NEC, and everyone else is under Under $600 Threshold.

Company drivers are not listed. W-2s are not supported, as the W-2 Generation card on this tab explains.

Settlements and Executive users can open the tab, but only Super Admin, Company Admin and Accounting users can generate or download 1099s.

Check TINs First

Each 1099 needs the recipient's TIN. The TIN column only says On File or Missing. It never shows the number, and TINs are masked on the PDF.

For a driver, click Edit under Personal Information on the driver's Profile tab and fill in Social Security Number in the Employment section. The number is stored encrypted and shown masked.

CloudTMS does not stop you from generating a 1099 when the TIN is missing, so check this column before you generate. Fleet owners always show Missing because CloudTMS doesn't store a fleet owner TIN yet.

Generate and Download

The PDF is a recipient copy for your records and for your contractors. CloudTMS does not file with the IRS for you. File through your own tax software or an authorized e-file provider. For questions about what to report, check with your tax professional.

  1. Open Settlements → Year-End / 1099s and choose the Tax year. (page: /settlements?tab=year-end)
  2. Click Generate on a row, or Generate all (N) for every eligible recipient. Click Regenerate after correcting settlements so the 1099 picks up the new total. (page: /settlements?tab=year-end)
  3. Click PDF on a row to download one, check rows and click Download N selected, or click Download all (N) for a ZIP of every generated 1099 for the year. (page: /settlements?tab=year-end)

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